Till Death Us Do Part

Low-lit and immaculate, with floor-to-ceiling windows overlooking the tony Back Bay neighborhood, and waiters semi-fluent in French (or at least the accent), upscale Boston restaurant L’Espalier is a special-occasion destination. Engagements are par for the multi-course, and longtime maître d’ Louis Risoli estimates he’s been witness to more than 1,000 during his 30-odd years at the front of the house. In recent years, though, they have taken a decidedly dramatic turn.

“The engagement I remember most was when the gentleman excused himself and left the restaurant for a fairly long time,” says Risoli. “He returned in a full suit of armor, as her knight in shining armor, and presented the ring to his beloved.”

Another memorable proposal went down as a guy placed an iPod on his table, played their song, and handed Risoli a large video camera before getting down on one knee in front of a crowded dining room. “It was actually a bit embarrassing for everyone except for him,” says Risoli. “His girlfriend seemed quite uncomfortable.”

It’s not enough anymore to whisk a girl away for a quiet weekend to pop the question, or pull the old hide-the-ring-in-the-parfait trick. These days, grooms are getting creative—in some cases, ridiculous—in the name of impressing their would-be wives: proposing atop an elephant in the Thai jungle, at mile 18 of the New York City Marathon, while faking their own death (true story) and, most crucially, in front of lots and lots of people.

“I knew it had to be memorable, and that it had to be public,” says Dennis Gleason, a Portland, Oregon–based television host, of his proposal to M’chel Bauxal, a celebrity makeup artist. For one thing, he says, “a basic proposal would be considered insignificant to some of her elite clientele.” So he devised a ruse to have her appear as an emergency guest on his show, enlisted the help of the entire crew, and proposed on live TV.

“Unlike almost everything else related to weddings, the parameters aren’t already set for the proposal,” says Los Angeles publicist Matt Paget, who proposed to girlfriend Morgan O’Malley by planting an illustration drawn by her architect father on one of her favorite websites, Postsecret.com. “You can take more liberties with it.”

But everyone knows that men aren’t, very generally speaking—and Paget excepted—the more creative half of a twosome, a fact that has given rise to a new breed of expert specializing in crafting the perfect, and perfectly extreme, proposal: the proposal planner.

“The majority of women aren’t satisfied with their marriage proposal,” says Michele Velazquez, a former corporate event planner who launched her Los Angeles–based proposal planning business, The Heart Bandits, after her own disappointing “ask” aboard a sunset cruise through Marina del Rey. “He actually had this list of many awful ideas, including hiring a clown,” she says of her fiancé. “I hate boats, but apparently that was his best choice.”

While Velazquez and her team also plan other romantic occasions (anniversaries, first dates), proposals represent 95 percent of her business (September through January is the busiest season, she says). The team generally works with high-end clients who don’t have time to, say, hire a helicopter or figure out where to get and how to release doves, or who, like one groom, envision the perfect proposal as one that includes a flash mob and a skit from How I Met Your Mother. For that client, Velazquez hired a professional choreographer and two professional dancers and scouted the ideal Manhattan rooftop location. A proposal package can cost anywhere from $ 3,000 to more than $ 10,000, including execution and, if necessary, props, because doves are not free.

“Social media has a huge part in why proposals are getting so grand,” says Velazquez. “You put it on YouTube and 10 million other women see it, and they want their proposal to be as unique as that.”

Paget says that for him, it was more about creating something permanent, and personal. “What I do for a living definitely informed my approach,” says Paget. “I targeted my audience: Morgan. I figured out the tools I had to reach her with: the website. I did not sleep the night before. And it was probably the best thing I’ve ever done.” Naturally, she said yes.

Of course, with a huge proposal, you run the risk of a huge rejection. Among major buyers of fine jewelry, watches and diamonds, Circa is the top buyer in bling you just don’t want to look at anymore. In-house experts will consider quality, cut, whether it’s inscribed, and where and when you bought it to give you a fair price. (Don’t worry: They won’t make you talk about what went wrong.) The best part is that in most cases, you’ll walk away with a check the same day. Says Angelina Chen, director of Circa’s New York office, “I imagine in a situation like that you’d welcome a swift resolution.” circajewels.com

Low-lit and immaculate, with floor-to-ceiling windows overlooking the tony Back Bay neighborhood, and waiters semi-fluent in French (or at least the accent), upscale Boston restaurant L’Espalier is a special-occasion destination. Engagements are par for the multi-course, and longtime maître d’ Louis Risoli estimates he’s been witness to more than...